Luxury Properties for rent in Osterville, Massachusetts

Welcome to your ideal summer retreat at 360 Main St, Osterville. This exceptional property offers everything you need for a luxurious and relaxing stay. Enjoy the stunning outdoor...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Spend your Cape Cod vacation in this magnificent property located on Garrison Lane in Osterville. Enjoy your days relaxing by the private pool surrounded by professionally...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

This home is located in the heart of Wianno, only minutes to Dowses Beach and the village of Osterville. The first floor offers an open floorplan including living room, dining,...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

236B Smoke Valley is serene and surrounded by nature, offering peaceful mornings, beautiful sunsets, and water access right outside your door. A deep-water pier and float can...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Cape Cod summertime magic awaits at this classic shingled charmer in the heart of Wianno. Just moments from Osterville Village and Dowses beach, and superbly appointed, everything...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Welcome to Seasons by the Sea! This fully remodeled Osterville home offers four bedrooms, three and a half baths and all the outdoor living space for a perfect beach vacation....

Presented by Jan Macallister | Sotheby's International Realty - Osterville Brokerage

Coastal charm at its best. This home is a short stroll to Osterville Village and Dowses Beach, sits on an expansive lot with plenty of room for backyard play. A sizeable...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Pretty Osterville ranch in the heart of Wianno. This home is just moments to Main Street's fine restaurants, shops, library and beautiful Dowses Beach. Features include three...

Presented by Joanne Murphy | Sotheby's International Realty - Osterville Brokerage

Osterville Summer Rental! $2500/week or minimum of three-night stay; please call for nightly and off-season rates! This Osterville home is uniquely styled with fine furnishings...

Presented by Marina Davalos | Sotheby's International Realty - Osterville Brokerage

Welcome to 147 Scudder Road in Osterville! This charming rental offers the perfect blend of convenience and relaxation, just a short stroll away from Main Street and the pristine...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Spring, summer, fall rental. Not available as a yearly rental. In the heart of Osterville - this pretty Ranch features two bedrooms (a master with private bath and full bed), a...

Presented by Joanne Murphy | Sotheby's International Realty - Osterville Brokerage

Escape to one of Cape Cod’s most coveted neighborhoods with this beautifully renovated 5-bedroom, 5-bath home in Wianno. Perfect for family gatherings or a relaxing getaway, this...

Presented by Gene Orloff | Sotheby's International Realty - Osterville Brokerage

Spring, summer, fall rental. Not available as a yearly rental. Just a quick stroll to the village and 1.24 miles to the beach. This pretty Ranch features three bedrooms (two...

Presented by Joanne Murphy | Sotheby's International Realty - Osterville Brokerage